Method for producing aryl compound containing tritylsulfanyl group

Abstract

The present invention provides: a substrate for efficiently synthesizing a tritylsulfanyl group-containing aryl compound; a method for producing an SF5 group-containing compound using the same; and the like. The present invention is a method for producing a tritylsulfanyl group-containing aryl compound, the method including thiotritylation of a halogenated aryl compound represented by the following general formula (1) [wherein A1 is an aryl group which may have a substituent or a heteroaryl group which may have a substituent; and X is a halogen atom] using [(triphenylmethyl)sulfanyl]potassium or [(triphenylmethyl)sulfanyl]sodium to produce a tritylsulfanyl group-containing aryl compound represented by the following general formula (2) [wherein A1 is the same as A1 in the general formula (1); and Ph is a phenyl group].

1 . A method for producing a tritylsulfanyl group-containing aryl compound,
 the method comprising   thiotritylation of a halogenated aryl compound represented by the following general formula (1) using [(triphenylmethyl)sulfanyl]potassium or [(triphenylmethyl)sulfanyl]sodium,   
       
         
           
           
               
               
           
         
         [wherein A 1  is an aryl group which may have a substituent or a heteroaryl group which may have a substituent; and X is a halogen atom] 
         to produce a tritylsulfanyl group-containing aryl compound represented by the following general formula (2): 
       
       
         
           
           
               
               
           
         
         [wherein A 1  is the same as A 1  in the general formula (1), and Ph is a phenyl group]. 
       
     
     
         2 . The method for producing a tritylsulfanyl group-containing aryl compound according to  claim 1 , further comprising
 thiotritylation of the halogenated aryl compound represented by said general formula (1) using a palladium catalyst.   
     
     
         3 . The method for producing a tritylsulfanyl group-containing aryl compound according to  claim 2 , wherein said palladium catalyst is Pd[cinnamyl]( t BuXPhos)OTf or Pd[allyl](AlPhos)OTf. 
     
     
         4 . The method for producing a tritylsulfanyl group-containing aryl compound according to  claim 1 ,
 wherein said A 1  is   an aryl group which may have one or more substituents selected from the group consisting of a halogen atom, an alkyl group, a fluorinated alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, a hydroxy group, a carboxy group, an acyl group, a cyano group, a fluorinated formyl group, an amino group, a nitro group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a pyrazolidinyl group, an imidazolidinyl group, a tetrahydrofuranyl group, a 1,3-dioxolanyl group, a tetrahydrothiophenyl group, a 1,2-oxathiolanyl group, a morpholinyl group, and a tetrahydropyranyl group, or   a heteroaryl group which may have one or more substituents selected from the group consisting of a halogen atom, an alkyl group, a fluorinated alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, a hydroxy group, a carboxy group, an acyl group, a cyano group, a fluorinated formyl group, an amino group, a nitro group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, a pyrazolidinyl group, an imidazolidinyl group, a tetrahydrofuranyl group, a 1,3-dioxolanyl group, a tetrahydrothiophenyl group, a 1,2-oxathiolanyl group, a morpholinyl group, and a tetrahydropyranyl group.   
     
     
         5 . The method for producing a tritylsulfanyl group-containing aryl compound according to  claim 1 ,
 wherein a reaction of said thiotritylation is carried out at 0 to 80° C.   
     
     
         6 . A method for producing a pentafluorosulfanyl group-containing aryl compound,
 the method comprising:   producing a tritylsulfanyl group-containing aryl compound represented by said general formula (2) from a halogenated aryl compound represented by said general formula (1) by the method for producing a tritylsulfanyl group-containing aryl compound according to  claim 1 ; and   synthesizing a pentafluorosulfanyl group-containing aryl compound represented by the following general formula (3) from said tritylsulfanyl group-containing aryl compound by an oxidative fluorination reaction using a divalent or higher metal fluoride and an organic salt containing a quaternary ammonium cation or a quaternary phosphonium cation   
       
         
           
           
               
               
           
         
         [wherein A 1  is the same as A 1  in the general formula (1)]. 
       
     
     
         7 . The method for producing a pentafluorosulfanyl group-containing aryl compound according to  claim 6 ,
 wherein said oxidative fluorination reaction is carried out at −40 to 130° C.